An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

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Check availability on Middlesboro Hotels with Pool

Our top choices for Middlesboro hotels with a pool

Outdoor pool, pool loungers

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (727 reviews)
  • cleanliness
    Splash into mountain adventures with a sun-kissed pool oasis featuring comfy loungers for peak relaxation.
The price is ฿3,688
฿4,065 total
includes taxes & fees
2 Aug - 3 Aug
Holiday Inn Express Middlesboro by IHG
Single Room, 1 Queen Bed, Smoking | Bathroom | Free toiletries, towels

Boone Trail Inn

Boone Trail Inn
2.0 star property
Middlesboro
7.4 out of 10, Good, (118 reviews)
  • cleanliness
    Dive into summer adventures with a seasonal outdoor pool, perfect for relaxing after a day exploring nearby hiking trails.
The price is ฿2,691
฿3,557 total
includes taxes & fees
16 Jul - 17 Jul
Boone Trail Inn
Seasonal outdoor pool

Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
Middlesboro
8.2 out of 10, Very good, (96 reviews)
  • cleanliness
    Escape the ordinary at this freshly remodeled hotel with a sparkling seasonal pool and newly updated rooms for summer relaxation.
The price is ฿2,623
฿2,891 total
includes taxes & fees
12 Aug - 13 Aug
Suburban Studios Middlesboro
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool loungers

Econo Lodge Middlesboro

Econo Lodge Middlesboro
2.0 star property
Middlesboro
7.4 out of 10, Good, (491 reviews)
  • cleanliness
    Pristine mountain retreat offers seasonal poolside bliss with lounge chairs for a perfect summer escape in Middlesboro.
The price is ฿2,893
฿3,190 total
includes taxes & fees
19 Jul - 20 Jul
Econo Lodge Middlesboro
Indoor pool

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Dive into poolside relaxation at this clean, comfortable hotel with an indoor oasis just steps from Kentucky Splash Water Park.
The price is ฿3,219
฿3,583 total
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Williamsburg by IHG
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (735 reviews)
  • cleanliness
    Refreshing mountain escape with a seasonal outdoor pool surrounded by loungers, umbrellas, and panoramic Appalachian views.
The price is ฿5,122
฿5,646 total
includes taxes & fees
31 Jul - 1 Aug
Pine Mountain State Resort Park
Business centre

Quality Inn

Quality Inn
2.5 star property
Barbourville
8.2 out of 10, Very good, (276 reviews)
  • cleanliness
    Outdoor pool beckons with refreshing dips and sun-soaked lounging at this welcoming hotel.
The price is ฿3,074
฿3,486 total
includes taxes & fees
9 Aug - 10 Aug
Quality Inn
Aerial view

Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
3.0 star property
Tazewell
9.2 out of 10, Wonderful, (151 reviews)
  • cleanliness
    Seasonal lakeside golf retreat with picturesque course, outdoor pool, and tennis courts offering serene relaxation in nature.
The price is ฿5,525
฿6,202 total
includes taxes & fees
16 Jul - 17 Jul
Woodlake Lodge Golf and Country Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Middlesboro

Breakfast included
Hot tub

Top Middlesboro Hotel Reviews

Econo Lodge Middlesboro

Econo Lodge Middlesboro

8/10 Good
"Rooms were clean, thankfully AC worked because we were hot and sweaty from moving my daughter into her apartment. Bathrooms were clean as well as the room."
Heidi 2-night trip
Posted 3 days ago
Econo Lodge Middlesboro

Frequently asked questions

What are some accommodation options with pools in Middlesboro?
Sleep Inn & Suites Middlesboro: Offers continental, a seasonal outdoor pool and free self parking. Econo Lodge Middlesboro: Provides buffet, an outdoor pool and free self parking. Holiday Inn Express Middlesboro by IHG: Offers daily, an indoor pool and free self parking. Days Inn by Wyndham Jellico - Tennessee State Line: Provides daily, a seasonal outdoor pool and free self parking. Holiday Inn Express Williamsburg by IHG: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Middlesboro?
Spend some time experiencing the great outdoors at Kentucky Ridge State Forest. During your stay, visit sights such as Cumberland Gap National Historical Park, Middlesboro Country Club and Middlesboro Mall. Take in the natural beauty of Middlesboro with the mountain views.
When is the best time to book a hotel with a pool in Middlesboro?
You may want to consider a place to stay that has an outdoor pool if you plan to visit Middlesboro in the warmest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 5°C.